Windows does remember that certain USB devices (that are consistently plugged into the same USB port) are associated with a drive letter. These letters get shifted if, and only if, you add a new device and have your previous one unplugged. You can solve this problem by unplugging the new device and restarting, at which point plugging in your old device (in the same USB port) will give it its previous drive letter.

For instance, I have an external hard drive that is always drive G and is assigned drive G if i unplug and replug later.

It might indeed just be better to create empty folders and then mount drives to those folders. Create a 16MB or smth partition on a drive always in your PC, mount it to X, create some empty folders and then just mount your external drives to those folders. I think Windows should remember those, but I'm not sure. Then you can just use X:\USB1, X:\Data, X:\...

or maybe make it slightly easier to change the drive letter cause if you're using flash drives alot then having the ability to change the letter via a dropdown menu or on the auto play window would be very handy.

I agree. The other thing is, that a Mac allows you to move and rename files even while they are opened without applications losing their reference to the file. I'd like to see the same thing on Windows.

The idea to drop letters was one of the things they had in mind for the original longhorn but it got scrapped. Libraries sorta fix this but in the end we still have them and unless there's some deep file system changes we're stuck with them.

I agree that drive letters are a very poor way of organizing mounted partitions, but Microsoft probably can't change it at this point because switching from drive letters to folder mount points wholesale would break assumptions made by many programs - sacrificing legacy compatibility - which they won't do.

When a flash drive is inserted into a computer running OS X, Finder will automatically mount its partitions to /Volumes/Some Partition Name. If there is already a partition mounted at /Volumes/Some Partition Name, Finder will mount the partition to /Volumes/Some Partition Name 1 instead. Nautilus (the default file manager in Ubuntu) does something very similar, except partitions are mounted to /media/Some Partition Name and conflicts are resolved by appending (number) to the end of the mount point. Therefore, so long as the label of the partition on your flash drive is sufficiently unique, you can reasonably expect that it will be mounted in the same place no matter which USB port you plug it into or which Mac you use.

As others have already mentioned, Windows also allows you to mount partitions to folders - which might solve your problem - but I'm not sure if those mount points are persistent. Based on the way that Windows remembers drive letters (which billyea nailed in the first reply), I would guess that it behaves similarly for folder mount points.

If you have a specific thumb drive that has apps you want to create shortcuts to, go into Disk Management and manually change the drive letter to either A or B. These drive letters are normally reserved for legacy disk drives, so no USB drive will automatically take that letter (unless it is an actual floppy drive), even if your A/B thumb drive is not there.

I've tried it out, and it seems to work. I guess Windows can recognize each thumb drive as unique.

It would be nice if they made shortcuts and drive mapping more automatic and easier, though.

Win RT uses the same drive letter format, however, Applications only have access to local locations (thisApp.folder/myfile.txt) or libraries, so Microsoft could remove drive letters completely without sacrificing backwards compatibility at some point in the future.